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Volumn 55, Issue 5, 2012, Pages 2067-2077

A click chemistry approach to pleuromutilin derivatives, part 2: Conjugates with acyclic nucleosides and their ribosomal binding and antibacterial activity

Author keywords

[No Author keywords available]

Indexed keywords

22 (1,2,3 TRIAZOL 1 YL) 22 DEOXYPLEUROMUTILIN; 22 [4 (2 THYMIN 1 YL)ETHOXYMETHYL) 1,2,3 TRIAZOL 1 YL] 22 DEOXYPLEUROMUTILIN; 22 [4 (2R (URACIL 1 YL) 4S HYDROXY 5R HYDROXYMETHYL)TETRAHYDROFURAN 3R YLMETHYL) 1,2,3 TRIAZOL 1 YL] 22 DEOXYPLEUTOMUTILIN; 22 [4 (3 (ADENIN 9 YL)PHENYL) 1,2,3 TRIAZOL 1 YL] 22 DEOXYPLEUROMUTILIN; 22 [4 (3 (ADENIN 9 YL)PROPEN 1 YL) 1,2,3 TRIAZOL 1 YL] 22 DEOXYPLEUROMUTILIN; 22 [4 (3 (THYMIN 1 YL)PROPEN 1 YL) 1,2,3 TRIAZOL 1 YL] 22 DEOXYPLEUROMUTILIN; 22 [4 (4 (ADENIN 9 YL)PHENYL) 1,2,3 TRIAZOL 1 YL] 22 DEOXYPLEUROMUTILIN; 22 [4 (ADENIN 9 YLMETHOXYMETHYL) 1,2,3 TRIAZOL 1 YL] 22 DEOXYPLEUROMUTILIN; 22 [4 (BENZYLOXYMETHYL) 1,2,3 TRIAZOL 1 YL] 22 DEOXYPLEUROMUTILIN; 22 [4 (THYMIN 1 YLMETHOXYMETHYL) 1,2,3 TRIAZOL 1 YL] 22 DEOXYPLEUROMUTILIN; 22 [5 (3 (ADEN 9 YL)PROPYL) 1,2,3 TRIAZOL 1 YL] 22 DEOXYPLEUROMUTILIN; ACYCLIC NUCLEOSIDE; CARBENE; NUCLEIC ACID BASE; OXYGEN; PHENYL GROUP; PLEUROMUTILIN; RETAPAMULIN; TERPENOID DERIVATIVE; TIAMULIN; UNCLASSIFIED DRUG; VALNEMULIN;

EID: 84863242788     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201266b     Document Type: Article
Times cited : (36)

References (26)
  • 1
    • 0001581071 scopus 로고
    • Antibiotic substances from Basidiomycetes: VIII. Pleurotus multilus (Fr.) Sacc. and Pleurotus passeckerianus Pilat
    • Kavanagh, F.; Hervey, A.; Robbins, W. J. Antibiotic substances from Basidiomycetes: VIII. Pleurotus multilus (Fr.) Sacc. and Pleurotus passeckerianus Pilat Proc. Natl. Acad. Sci. U.S.A. 1951, 37, 570-574
    • (1951) Proc. Natl. Acad. Sci. U.S.A. , vol.37 , pp. 570-574
    • Kavanagh, F.1    Hervey, A.2    Robbins, W.J.3
  • 3
    • 0035788806 scopus 로고    scopus 로고
    • The pleuromutilin drugs tiamulin and valnemulin bind to the RNA at the peptidyl transferase centre on the ribosome
    • Poulsen, S. M.; Karlsson, M.; Johansson, L. B.; Vester, B. The pleuromutilin drugs tiamulin and valnemulin bind to the RNA at the peptidyl transferase centre on the ribosome Mol. Microbiol. 2001, 41, 1091-1099
    • (2001) Mol. Microbiol. , vol.41 , pp. 1091-1099
    • Poulsen, S.M.1    Karlsson, M.2    Johansson, L.B.3    Vester, B.4
  • 4
    • 33645767206 scopus 로고    scopus 로고
    • Interaction of pleuromutilin derivatives with the ribosomal peptidyl transferase center
    • Long, K. S.; Hansen, L. H.; Jakobsen, L.; Vester, B. Interaction of pleuromutilin derivatives with the ribosomal peptidyl transferase center Antimicrob. Agents Chemother. 2006, 50, 1458-1462
    • (2006) Antimicrob. Agents Chemother. , vol.50 , pp. 1458-1462
    • Long, K.S.1    Hansen, L.H.2    Jakobsen, L.3    Vester, B.4
  • 5
    • 9644281855 scopus 로고    scopus 로고
    • Inhibition of peptide bond formation by pleuromutilins: The structure of the 50S ribosomal subunit from Deinococcus radiodurans in complex with tiamulin
    • Schlunzen, F.; Pyetan, E.; Fucini, P.; Yonath, A.; Harms, J. M. Inhibition of peptide bond formation by pleuromutilins: the structure of the 50S ribosomal subunit from Deinococcus radiodurans in complex with tiamulin Mol. Microbiol. 2004, 54, 1287-1294
    • (2004) Mol. Microbiol. , vol.54 , pp. 1287-1294
    • Schlunzen, F.1    Pyetan, E.2    Fucini, P.3    Yonath, A.4    Harms, J.M.5
  • 7
    • 67349260439 scopus 로고    scopus 로고
    • U2504 determines the species specificity of the A-site cleft antibiotics: The structures of tiamulin, homoharringtonine, and bruceantin bound to the ribosome
    • Gurel, G.; Blaha, G.; Moore, P. B.; Steitz, T. A. U2504 determines the species specificity of the A-site cleft antibiotics: the structures of tiamulin, homoharringtonine, and bruceantin bound to the ribosome J. Mol. Biol. 2009, 389, 146-156
    • (2009) J. Mol. Biol. , vol.389 , pp. 146-156
    • Gurel, G.1    Blaha, G.2    Moore, P.B.3    Steitz, T.A.4
  • 8
    • 50249167106 scopus 로고    scopus 로고
    • A click chemistry approach to pleuromutilin conjugates with nucleosides or acyclic nucleoside derivatives and their binding to the bacterial ribosome
    • Lolk, L.; Pohlsgaard, J.; Jepsen, A. S.; Hansen, L. H.; Nielsen, H.; Steffansen, S. I.; Sparving, L.; Nielsen, A. B.; Vester, B.; Nielsen, P. A click chemistry approach to pleuromutilin conjugates with nucleosides or acyclic nucleoside derivatives and their binding to the bacterial ribosome J. Med. Chem. 2008, 51, 4957-4967
    • (2008) J. Med. Chem. , vol.51 , pp. 4957-4967
    • Lolk, L.1    Pohlsgaard, J.2    Jepsen, A.S.3    Hansen, L.H.4    Nielsen, H.5    Steffansen, S.I.6    Sparving, L.7    Nielsen, A.B.8    Vester, B.9    Nielsen, P.10
  • 9
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 2002, 67, 3057-3064
    • (2002) J. Org. Chem. , vol.67 , pp. 3057-3064
    • Tornøe, C.W.1    Christensen, C.2    Meldal, M.3
  • 10
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 11
    • 0017260288 scopus 로고
    • Studies on pleuromutilin and some of its derivatives
    • Riedl, K. Studies on pleuromutilin and some of its derivatives J. Antibiot. 1976, 29, 132-139
    • (1976) J. Antibiot. , vol.29 , pp. 132-139
    • Riedl, K.1
  • 13
    • 0034602325 scopus 로고    scopus 로고
    • Synthesis of tert -butoxycarbonyl (Boc)-protected purines
    • Dey, S.; Garner, P. Synthesis of tert -butoxycarbonyl (Boc)-protected purines J. Org. Chem. 2000, 65, 7697-7699
    • (2000) J. Org. Chem. , vol.65 , pp. 7697-7699
    • Dey, S.1    Garner, P.2
  • 15
    • 33751575313 scopus 로고    scopus 로고
    • Efficient N-arylation and N-alkenylation of the five DNA/RNA nucleobases
    • Jacobsen, M. F.; Knudsen, M. M.; Gothelf, K. V. Efficient N-arylation and N-alkenylation of the five DNA/RNA nucleobases J. Org. Chem. 2006, 71, 9183-9190
    • (2006) J. Org. Chem. , vol.71 , pp. 9183-9190
    • Jacobsen, M.F.1    Knudsen, M.M.2    Gothelf, K.V.3
  • 16
    • 33749122260 scopus 로고    scopus 로고
    • Analogues of a locked nucleic acid with three-carbon 2′,4′- linkages: Synthesis by ring-closing metathesis and influence on nucleic acid duplex stability and structure
    • Albæk, N.; Petersen, M.; Nielsen, P. Analogues of a locked nucleic acid with three-carbon 2′,4′-linkages: synthesis by ring-closing metathesis and influence on nucleic acid duplex stability and structure J. Org. Chem. 2006, 71, 7731-7740
    • (2006) J. Org. Chem. , vol.71 , pp. 7731-7740
    • Albæk, N.1    Petersen, M.2    Nielsen, P.3
  • 17
    • 84949695566 scopus 로고
    • Methanolysis of dimethyl (1-diazo-2-oxopropyl)phosphonate: Generation of dimethyl (diazomethyl)phosphonate and reaction with carbonyl compounds
    • Ohira, S. Methanolysis of dimethyl (1-diazo-2-oxopropyl)phosphonate: generation of dimethyl (diazomethyl)phosphonate and reaction with carbonyl compounds Synth. Commun. 1989, 19, 561-564
    • (1989) Synth. Commun. , vol.19 , pp. 561-564
    • Ohira, S.1
  • 18
    • 1542504084 scopus 로고    scopus 로고
    • An improved one-pot procedure for the synthesis of alkynes from aldehydes
    • Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. An improved one-pot procedure for the synthesis of alkynes from aldehydes Synlett 1996, 532-522
    • (1996) Synlett , pp. 532-522
    • Müller, S.1    Liepold, B.2    Roth, G.J.3    Bestmann, H.J.4
  • 19
    • 0037137588 scopus 로고    scopus 로고
    • Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1- (ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants
    • El-Brollosy, N. R.; Jørgensen, P. T.; Dahan, B.; Boel, A. M.; Pedersen, E. B.; Nielsen, C. Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants J. Med. Chem. 2002, 45, 5721-5726
    • (2002) J. Med. Chem. , vol.45 , pp. 5721-5726
    • El-Brollosy, N.R.1    Jørgensen, P.T.2    Dahan, B.3    Boel, A.M.4    Pedersen, E.B.5    Nielsen, C.6
  • 20
    • 31644447942 scopus 로고    scopus 로고
    • An efficient synthesis of acyclic N7- and N9-adenine nucleosides via alkylation with secondary carbon electrophiles to introduce versatile functional groups at the C-1 position of acyclic moiety
    • Kotian, P. L.; Kumar, V. S.; Lin, T. H.; El-Kattan, Y.; Ghosh, A.; Wu, M.; Cheng, X.; Bantia, S.; Babu, Y. S.; Chand, P. An efficient synthesis of acyclic N7- and N9-adenine nucleosides via alkylation with secondary carbon electrophiles to introduce versatile functional groups at the C-1 position of acyclic moiety Nucleosides Nucleotides Nucleic Acids 2006, 25, 121-140
    • (2006) Nucleosides Nucleotides Nucleic Acids , vol.25 , pp. 121-140
    • Kotian, P.L.1    Kumar, V.S.2    Lin, T.H.3    El-Kattan, Y.4    Ghosh, A.5    Wu, M.6    Cheng, X.7    Bantia, S.8    Babu, Y.S.9    Chand, P.10
  • 21
    • 27744526377 scopus 로고    scopus 로고
    • Highly regioselective palladium-catalyzed annulation reactions of heteroatom-substituted allenes for synthesis of condensed heterocycles
    • Inamoto, K.; Yamamoto, A.; Ohsawa, K.; Hiroya, K.; Sakamoto, T. Highly regioselective palladium-catalyzed annulation reactions of heteroatom- substituted allenes for synthesis of condensed heterocycles Chem. Pharm. Bull. 2005, 53, 1502-1507
    • (2005) Chem. Pharm. Bull. , vol.53 , pp. 1502-1507
    • Inamoto, K.1    Yamamoto, A.2    Ohsawa, K.3    Hiroya, K.4    Sakamoto, T.5
  • 22
    • 32244449190 scopus 로고    scopus 로고
    • Two simple protocols for the preparation of diallylaminoethyl-substituted nucleic bases: A comparison
    • Shatila, R. S.; Bouhadir, K. H. Two simple protocols for the preparation of diallylaminoethyl-substituted nucleic bases: a comparison Tetrahedron Lett. 2006, 47, 1767-1770
    • (2006) Tetrahedron Lett. , vol.47 , pp. 1767-1770
    • Shatila, R.S.1    Bouhadir, K.H.2
  • 23
    • 84863280655 scopus 로고    scopus 로고
    • Glide, version 5.7. Schrödinger, LLC, New York.
    • Glide, version 5.7. Schrödinger, LLC, New York, 2011.
    • (2011)
  • 25
    • 1642310340 scopus 로고    scopus 로고
    • Glide: A new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening
    • Halgren, T. A.; Murphy, R. B.; Friesner, R. A.; Beard, H. S.; Frye, L. L.; Pollard, W. T.; Banks, J. L. Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening J. Med. Chem. 2004, 47, 1750-1759
    • (2004) J. Med. Chem. , vol.47 , pp. 1750-1759
    • Halgren, T.A.1    Murphy, R.B.2    Friesner, R.A.3    Beard, H.S.4    Frye, L.L.5    Pollard, W.T.6    Banks, J.L.7


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